Pledging a Prestigious College Fraternity with the Help of a Sexy Crossdresser [MT]

I grew up in a small college city. A prestigious private university, a well-regarded state university, two small liberal arts colleges and a community college made for a very interesting environment.

Following high school I ended up attending that private university. After settling into classes, my friends and I began to attend some of the rush events hosted by fraternities tied to the different schools. The fraternities weren’t located on campus or on a fraternity row of any kind. They were located around town in areas largely populated by off-campus student housing.

It would have been absurd for me to actually pledge a frat. All locals were trained to dislike “frat boys” beginning at an early age. Joining a frat was unthinkable, but their beer was cold and free.

The parties were a lot of fun. Each frat house had its own character – and gang of characters that lived in them. My far the most prestigious frat in town was Delta Tau Omega (DTO) largely due to its beautiful building. The DTO structure was like a palace which had been sculpted out of marble – an edifice which had been requisitioned by a railroad executive in the late 1880s.

Mixing hiking a mountain and hot sex [MF]

Several years back I responded to a craigslist ad written by a woman wanting to “celebrate life” by “doing something out of the ordinary.” Because she had posted under “casual encounters” I presumed she was seeking something that included sex. Though she was a bit older than me (she was 47), the fact that she listed herself as 5’11” with an “athletic build” piqued my interest enough to respond to her listing.

Even though she had posted 17 days before, I still responded by telling her that I love to hike local mountains. I wanted to mix my love of hiking that with a nice lunch at the summit along with some physical intimacy.

She actually responded and she liked the idea. We spent the next several days trading anonymous craigslist emails describing our desires. When it came to trading photos, Fiona declined due to “professional reasons.” Normally that would be a red flag, but I enjoyed the dialogue which had become quite personal and erotic. The result was we finally decided to meet at the trailhead of a local mountain.

Other than her being fairly literate, 47, and 5’11” with an athletic body, I really didn’t know what to expect. I hadn’t even heard her voice.

[MF] My African Lover and I on a “Hell Train” through Mexico

As a college sophomore, my friends and I decided to take one of those cut-rate, spring break student trips on a train to Puerto Vallarta, Mexico — back when it was still safe to take such excursions. The drive from Los Angeles to Mexicali, MX gave some insight into what the trip was to be like — wild, drunken and gritty. Once we boarded the “hell train south”, things began to become more than a bit surreal.

While I had enjoyed my share of wild adventures by that point in my life, those spring-break junkets to Mexico were nothing more than drunken sex fests. While my three (male) friends I was traveling with were generally more conservative than I, they all jumped in with both feet on our way down south and began to party hard. I sensed a need to throttle back and I did – at least one of us had to keep our wits about ourselves in this foreign land.

[MF] Was your first time as off-the-wall good as my own?

I got lucky and made my HS varsity wrestling team as a sophomore. My HS had both male and female wrestling teams. The heavyweight on the girl’s team was an all-state senior. Her coach decided she needed someone her size to spar with so she made arrangements with my coach for her and I to drill after our respective practices.

At 6’3″ and #235 I had maybe 2-3″ and zero pounds on her. She had a reputation as being a good student, a big jock (she also played softball) and a thug of sorts. She was a black/Samoan mix with a rather beautiful face.

I was extremely nervous before our first training session given her experience, age and reputation. Two minutes into the session it was clear my physical strength and speed made it a horrible mismatch. Still, she was a very good technician, she was serious and it was a worthwhile learning experience for both of us.

After one session she said she needed to work on escapes and asked if I would spar with her again? I said sure — to meet me at the “state (university) wrestling room” tomorrow (Saturday) at ten AM. This room is always open during the season and unless practice is going on, anyone can use it to drill or cut weight.